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Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five‐Membered Heterocycles
Author(s) -
Cardoso Ana L.,
Pinho e Melo Teresa M. V. D.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200406
Subject(s) - chemistry , cycloaddition , nucleophile , ring (chemistry) , cleavage (geology) , aziridine , formal synthesis , bond cleavage , organic synthesis , combinatorial chemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
Chemistry based on ring opening of aziridines has been widely studied in organic synthesis. However, it has mainly been centered on ring opening by nucleophiles and on cycloaddition of azomethine ylides generated by carbon–carbon bond cleavage. In recent years, significant effort has been dedicated to study of the participation of aziridines in formal [3+2] cycloadditions, which provide routes for the construction of a wide variety of functionalized five‐membered heterocycles. Here we review the most relevant aspects of the reactivities and selectivities of aziridines as masked zwitterionic 1,3‐dipoles generated through C–N bond cleavage.